Why does the correct return address not show up on outgoing messages?

Hello,
Specs:
Windows NT
iPlanet Messaging Server 5.1
iPlanet Directory Server 4.13
One user recently went through an account change (spam reasons).
old uid: bob
old email: [email protected]
new uid: bsmith
new email: [email protected]
The problem is, that during testing, any email sent from the new account is arriving as having both the <Return-path> and <From> fields with the old email address.
Keep in mind that this is not a client-specific problem as everything has been changed correctly (outlook) If an email goes from "Clients computer" >> "3rd party smtp server" >> "Hotmail" or the like, it shows up as having the correct return address.
But the pickle I'm in, is that if an email goes from "Clients computer" >> "3rd party smtp server" >> "Our Server" , it shows up as having the OLD return address. - same thing if messages are sent internally (same server) through the webmail interface. The messaging server is somehow rewriting the email field when any message goes through it.
What makes this a super-pickle is that this is a NEW account., not just a 'change' of the old one. The old account has been deleted, and the command 'imadmin user purge' doesn't find it, nor is there any reference to the old 'bob@' address in the ldif file except for an address book entry or two (other users have added 'bob' into their address book)
Any help is greatly appreciated in advance. Sorry for the long description, but now all the bases I've covered are known.
Sincerely,
Josh

Jay,
I only mentioned SIMS 4.0 because I jumped directly from that to MS 6.0p1, and because what my customers wanted to do worked on SIMS and doesn't on MS6.
To complicate things more, my customer has multiple domains, but not all employees have e-mail addresses in both domains. For example, Joe is [email protected], Jane is [email protected], and John wants mail sent to either [email protected] or [email protected] to come to him.
I dealt with this by setting up abc & xyz as separate domains, and created a mailing list in xyz.com named "john" with an external member of [email protected] While this works fine, when I add an alias to that mailing list of "[email protected]" and John tries to send a message with "[email protected]" in the From, it is rewritten to [email protected] as that is his primary e-mail address.
In looking at the LDAP entries of mailing lists that are not working as I'd like, I see that the aliases are specified as mailAlternateAddress attributes. Are you saying that if I change these to MailEquivalentAddress attributes that they will then show up in the From unchanged?
Oh, and one more possible factor - they are sending mail using SMTP AUTH as they are roving users. Since the mail server knows that the authenticated user is truly [email protected], is that why his From of [email protected] gets nuked?
Thanks,
Bill

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